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In this episode, Jack is joined by Steve Shimizu, the CFO of Omnissa. They discuss Omnissa’s role in enabling digital employee experiences—helping companies support employees working from anywhere, on any device, across physical and virtual endpoints. Steve explains the CFO’s challenge in a carve-out: building standalone finance infrastructure while simultaneously positioning the company for profitable growth. The conversation also covers how Steve’s career chapters—from public accounting and IPOs to software M&A and operational finance—prepared him to lead through transformation. Steve shares how finance can drive better decisions by translating SaaS metrics into tangible, actionable insights and reinforcing accountability. He also reflects on resilience shaped by early sports injuries, and the importance of long-range planning, investing in innovation, and creating growth opportunities for employees. Thanks to our sponsors Bill https://www.bill.com/lp/procurement?u... and Intuit QuickBooks https://quickbooks.intuit.com/money/ Video Timestamps & Titles 0:00 — A Carve-Out That Feels Like Flying a 747 1:16 — Setting the Table: When Finance Must “Grow Up Fast” 2:22 — Welcome & The Throughline: Rigor Meets Strategic Judgment 3:18 — Career Chapters: Public Accounting, IPOs, and Early Direction 4:45 — Learning to Distill: Data Rooms and Decision-Ready Takeaways 6:10 — From Transactions to Operations: The “Two-in-a-Box” Lesson 7:57 — From VMware to Omnissa: A Divestiture Within an Acquisition 9:11 — Why Carve Outs Happen: The “Sub-Optimized” Hypothesis 10:05 — Phase One: Building Standalone Infrastructure at Scale 11:10 — Phase Two: Transformation After Stabilization 11:59 — What Omnissa Does: Digital Employee Experience Explained 14:31 — Growth vs. Discipline: The Case for Profitable Growth 16:42 — Finance as Proactive Partner: Making Metrics Actionable 20:03 — Defining Success: Decisions, Accountability, and Momentum 22:39 — AI: Leverage vs. Noise in Real Operating Terms 26:02 — Measuring ROI: Productivity, Pipeline, and Customer Support 30:07 — Finance Strategic Moment: EQ, Relationships, and Judgment 35:30 — Resilience Story: Injuries, Fortitude, and the Process 37:22 — Book Pick: John Wooden and the Pyramid of Success 38:41 — The Next 12 Months: Long-Range Planning, People, Innovation